Hello Rik! What's your background, and what are you currently working on?

Hi there Rich, thanks for taking the time to hear our story! I’m a fan of your work at Failory and enjoy learning from the other entrepreneurs.

Currently, my business partner Antonio (Ari) Iaccarino and I have launched Ridj-it , an online carpool platform for outdoor enthusiasts, matching those who need a ride to outdoor adventures (think hiking, skiing, camping, horseback riding, wine tasting, rock climbing, yoga, kayaking, rappelling, and even axe throwing!) with someone who can get them to these destinations and back. So far, this endeavour has definitely not been a failure like KnowNet (which I will get to shortly!), and in fact, we’ve seen substantial growth in the number of users and overall use in the last few months. We are operating out of the Boston area and look to expand to other East Coast cities.

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Before jumping into the KnowNet debacle, I’d like to touch upon how we arrived at Ridj-it - I think it will be a good way to introduce ourselves and offer an insight into what makes us tick. Ridj-it was an idea that we conceived on the way back from a hiking trip in the White Mountains in my then car, a 1997 Camry that graciously did not fall apart despite the more than 300,000 miles it racked up or from whatever was causing the repetitive popping noises on the rear right (or the entire rear, if we are being honest). At the time, I was going to grad school at night, studying epidemiology and biostatistics while working full time as a medical researcher, and Ari was an adjunct professor teaching ESL students in several schools and also tutoring. An escape to the outdoors was a welcome break from our crazy day-to-day routine, plus we loved hiking. After bagging three peaks in a grueling hike, Ari and I mused about how our hiking trips were really just limited to us and anyone else who could hitch a ride with me. Ari opined that at least only a few souls had to put up with my terrible music playlist, which consisted of whatever Boston stations that could still be salvaged as we went North on I-93, a rock station that kept playing old Green Day and The Offspring, or any other frequencies of garbled, static-y mix of bluegrass, sports radio, and Bible recitations. He made a good point.

Ari then posed a curious question: how does someone like his students, who are internationals without American driver’s licenses and awareness of the area’s outdoor offerings but who enjoy activities like hiking, able to easily get to the Whites for a hike? I pondered for a bit but couldn’t provide an answer and neither could he, which is rare because both of us have a lot to say about everything. I then thought about my grad student friends who enjoyed hiking, and it turns out that they relied on me, both for access and awareness. So, if I were to not go hiking, nor could they. I also reflected on various meetups, social and outing clubs, and college organizations - the traditional gatekeepers to these types of activities; true, these groups do enable organized hiking events, but everything is on the group leadership’s terms, the events for many of these groups are relatively infrequent, membership can be pricey, and there’s no reliable and consistent transit available apart from hoping someone would offer a ride or on the off chance that one of the groups booked a bus or van. We learned later that these groups are often steeped in unwelcoming social cliques and layered in unnecessary top-down bureaucracy, making accessibility to the outdoors even more untenable for folks like Ari’s students and my friends. But it wasn’t just internationals and grad students with large barriers to entry; a lack of reliable and consistent transport from an urban core like Boston to various popular destinations in far-flung places like a trailhead in the Whites would also impact a large percentage of urban dwellers, which includes those who have eschewed car ownership as a necessity of city living, people of color who have been systematically deprived from accessing and enjoying outdoor recreation, and young, transient professionals who find owning a car to be unnecessary and costly.

Through various conversations with each other, we asked ourselves the following: What if we could provide both a direct link and a bypass via an online platform that fosters a reliable and consistent (and affordable) transport program to hard-to-reach outdoor destinations and a network to folks that share similar hobbies, that doesn’t require engaging the tribal ingroup/outgroup politics of the gatekeepers? We agreed to bring this concept to fruition over burgers and milkshakes at our post-hike go-to diner in New Hampshire. Two years later, after research, experimentation, and refinement of our concept, Ridj-it has a fully functioning website with an active and growing user base, a great deal due to Alex Nikitin, who joins Ridj-it as a co-founder and lead developer, and to Liz, Nick, and John for their help in marketing, product development, and graphic design. Ridj-it was named after Franconia Ridge, the trail that we hiked that day.

While working on growing Ridj-it and ensuring that it fulfills its mission, I also work full time as a data analyst in the healthcare space, Ari is a public school teacher, and Alex is a software developer at a local university.

Prior to our work with Ridj-it, Ari and I also embarked on an idea for an on-demand tutoring platform called KnowNet. The idea, which came to us about four years ago, was to enable those who needed tutoring to quickly find a tutor to offer guidance for an issue that the former encountered during the course of study. KnowNet never took off because a simple SWOT analysis revealed that there were too many competitors with advanced products and VC backing. We failed before we could even begin.

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What was KnowNet about?

KnowNet was born from our experiences as tutors. Ari and I both tutored extensively - he primarily served the ESL (English as a Second Language) community both as a tutor and university/public school classroom instructor, and I tutored high school and college students in Math and Sciences, in addition to my day job at the time as a multiple sclerosis researcher.

Ari and I would touch base with each other about our students’ progress and our styles of teaching. Over time, we realized something: though our subject areas were different, there was a notable pattern with both of our groups, which for a lack of a better term, we called the “threshold effect.” And for a lack of a better definition, we proposed that the “threshold effect” was when a student transitions from not understanding a particular concept (especially one where much effort had been applied) to understanding that particular concept, and they additionally overcome a cognitive block whereby many related concepts suddenly make sense when they hadn’t before. In other words, the understanding of that one hard-to-grasp concept led to a global understanding of the subject in unison. We noted that the student’s overall performance in the subject also improved following the “threshold effect.”

Given the all or nothing outcome of the “threshold effect”, we posited that optimal tutorial help could come at a point, during the course of studying or doing homework, when a student was near but had not overcome the threshold. So, if a student is studying and needed that immediate extra bit of help in understanding a concept to cross that threshold, we reasoned that a platform with on-demand tutorial services could have a positive outsized impact on the student’s performance in a class or subject. That then was our motivation for KnowNet.

The tutoring sessions would have been conducted online through the KnowNet platform, with built-in online whiteboards and video streaming capabilities. But that was the extent to the details of the platform that we had vetted out before calling it quits. We had not come up with a pricing model, nor had we even broached upon the nuances of how interaction would take place between the student and the tutor.

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What were your marketing plans to grow KnowNet?

We, of course, did not get to a point beyond the idea stage with KnowNet, so we never got a chance to grow the business. Our initial plan was to reach out to nearby students through our contacts in the area, but before we could do that, we in fact needed tutors who were willing to participate (having the supply ahead of time before meeting demand), which was a fact that we didn’t appreciate at the time. In fact, with Ridj-it, the analogy was to actively pursue and market to drivers to ensure they were available to provide rides. Also, to reach students, we were aware that we had to market to their parents or caretakers, and so our marketing strategy would’ve included targeted mail campaigns to residences near schools, for example, or advertised to well-known blogs devoted to parenting (i.e., mommy blogs) and education. As a way to bring in tutors, we considered the prospect of offering tutoring companies a devoted place on the platform, as a marketplace for them to cast a wider net and get newer clients.

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What was the problem with KnowNet? How did you realize this?

At the time, we stopped working on the idea because there were too many competitors who had VC backing, paying customers, and were in incubators. We went to work on fleshing out the high-level details of KnowNet before Ari suggested that we conduct a SWOT (Strengths, Weaknesses, Opportunities, and Threats) analysis, something he picked up through his university course Management for English Schools course. We spent about two hours identifying threats and we found a handful of very impressive platforms that more or less did what we had come up with. Needless to say, we were quite deflated at having our idea shot down so quickly, but in hindsight, we realized it was a very safe form of failure.

We also realized later after our work with Ridj-it that it was OK if there was another business out there that has already taken our idea; in a world of 7.5 billion people, this notion should not be a surprise. Implementation, marketing, tailoring your product to bring repeating enthusiastic customers, and a bit of luck are all rather important, and a budding entrepreneur should consider those factors too and not solely whether a similar product is already available. What also prevented us from moving forward, while we wouldn’t necessarily understand it four years ago, was our lack of experience and skillsets in tech at that point plus the lack of funds.

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What were the mistakes you made?

I think we were trying to bite off more than we can chew without fully appreciating the type of effort and know-how that was required for running a startup. We simply did not have the skillsets at the time to bring the idea to a product, and we also did not have the funds or resources to obtain that type of help; the SWOT analysis saved us from learning this the hard way. With Ridj-it, we found that having access to money and being good at managing money, having work experience, and ability to pick up skills as needed were important predictors of success. Our mistake, apart from trying to competing with established competitors, was not being prepared enough to manage a start-up.

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What were your biggest disadvantages?

The two biggest disadvantages for us were: 1) not having the proper skillsets or maturity to implement and run KnowNet, 2) several big competitors.

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If you had to start over, what would you do differently?

No. This was a necessary fail for us. It was a learning experience and it was humbling.

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What did you learn?

I learned:

Always do a SWOT analysis.

If there are a lot of competitors, do not let it be the only reason to end the venture. It should be considered in conjunction with other potential issues.

Start by implementing the idea with the lowest tech possible to achieve the desired business goals, and start scaling and refining after learning about the particular needs of the customers.

A certain level of preparedness and maturity is needed.

What's your advice for someone who is just starting?

I have 3 pieces of advice:

Find some to talk to about your idea. Someone you trust and whose opinion you value. Don’t bottle it up inside because you’re scared they’ll steal your idea. They won’t.

This might be trite, but make sure to focus on your MVP, and how you can make a barebones version of your ideal that you can bring to market.

It is important to really want your idea to succeed, but make sure to make time to be around the people who are important to you and to partake in activities that make you happy. There is no pride in working 80+ hours a week for the sake of working 80+ hours a week.

Which startup book would you recommend?

I’d say The Lean Startup by Eric Ries. He provides intricate details of his experience working on various startups, and drew lessons upon his failures. Another source is Marketing Outrageously by Jon Spoelstra, which is a bit gimmicky but has fairly good points about how conservative marketing isn’t a good fit for new companies.